One of the many legacies left to us through ancient Greek literature is the concept of mentoring. The ideal mentoring relationship involves three key components: (1) Continuing to carry out other duties while assuming the care-giving role; (2) Serving as a conduit for the wisdom of others; and (3) Developing a long-term connection. Mentoring can help at-risk youth develop their identities and decision-making skills. However, it may require gradual movement through the early trust-building stages (i.e., trust versus mistrust; autonomy versus doubt; initiative versus guilt; industry versus inferiority; identity versus identity confusion; intimacy versus isolation). At-risk youth often go through these stages in new environments, community-based programs, and mentoring relationships. Working on the issues and moving someone through this process takes time, patience, and understanding. This model program demonstrates the challenges and power of mentoring relationships between educators and students at risk. (Contains 1 note.)